The synthetic utility of S-mesitylsulfinimines for the synthesis of chiral amines and aziridines was examined through their reactions with Grignard reagents, with the ylides derived from trimethylsulfonium iodide and S-allyl-tetrahydrothiophenium bromide and through an aza-Darzens manifold, affording convenient access to a diverse range of highly substituted chiral amines and aziridines in high yields and excellent stereoselectivities.

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On the Utility of S-Mesitylsulfinimines for the Stereoselective Synthesis of ChiralAmines and Aziridines. -The S-mesitylsulfinimines are a useful alternative. In comparison to tert-butylsulfinimines, larger nucleophiles can be used and in comparison to the para-tolylsulfinyl group the S-mesitylsulfinyl group can be removed from aziridines by mild acidic conditions. Furthermore, they are readily available and UV active. -(ROE, C.; SOLA, T. M.; SASRAKU-NEEQUAYE, L.; HOBBS, H.; CHURCHER, I.; MACPHERSON, D.; STOCKMAN*, R. A.; Chem. Commun. (Cambridge) 47 (2011) 26, 7491-7493, http://dx.